Fall 2004 test 3 - H Hut Didi ‘7“ I3{Escsmc flamers-Y...

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Unformatted text preview: H Hut: Didi ‘7“ I3 ,. {Escsmc flamers-Y FALL 2034 M Asst Dr. Wefls . 2 Name: KB I 5m“?— th't ? Score = opscan*9tif25 + essa},r = S * QWES + 10 = It} With-1 i unit; (1:3 flt'hmi‘a, Essay 1D pts. The addition of deuterium bromide to propene gives two alkyI bromide products. Dean.r the two products; indicate which is major. Write the mechanism For the addition. Be sure to indicate intermediates with {1. Show how two products are formed and explain why one is dominant. tir‘eHLtcid t it H H Nukfi‘imlk‘u ts; _ [/Ewrw'ntr‘Kw 3 r. (:3 f DIN C9 D D p“ . M 1,1 \ (IE) I" 'rr 1 ® \ H t #14 H— L—fliflr-L'“ __.r;, VIN-'3' ._.——-C}:. i i: 1" IL H rt i4 H ‘i/ [hr #3 H b F? Vi i \ H I, é—flr” nesflc'“‘" H’T w * fa Jr A p. I'm. H Ch" 5ka mcr‘ibJ‘“ ‘11:” mm: Km} 'M. iii-M \TQ\I WW Wot" ‘4 to T3 ~ Sesame EHEMIsTaY FALL 2331] Dr. Wells 3 5 Name; Rear Seore = ops-nan * SPIRES + essay = " Eifir'flfi + H3 = “3'3 Noel! mm 100- who a. broad Essay 1i] pts. The elimination of hydrogen chloride From 2-ohioro-3-methylhutaoe by lithium diisopropyl amide [IDA] gives two alkene products. Draw the two products; indicate which is major. Write the mechanism for the elimination. Be sure to indicate transition states with Eli. Show how two produots are formed and explain 1W.“ MW 6 GD H Elf- “I {I 1| [J l t "< Ll H ——r_ -—-« c. -* C.“ me i i 1 A 1 . H Li H H gin” : t H : l I 1 MC- H_o——L—‘—. (L—-i"1c H H [Me in P: Fl": e H H x 1 1 H“f‘%mfiww HfYHLZfi~W H a m Wt" a L m him klfl¥rflnfifi predeb'll Ehl‘l'jeil {h hinge-1 A} c3) 0) B] C) D} E} LgJ B} C} D} E} __ (J'lHEK Uéfflh“5 fiihilaf -# The eorreet [UPAC name for the following compound is: Br I nag-on—ong—fi~ea2—cag CH2 ZrBromo-tl-methylenehexane 2-{2-Broniopropyljr1-butene 4-H romo-E—etltyl-l -pentene 2-Hrcmo4hethyI-l-pentene 2-Hrorno4~elhyl4-pentene The correct IUPAC name for the following compound is; Br CH2CHCH3 | CH3 {E)-2-Eromo-3 -chloro—5—mefltyl—2—hexene {E)-2-Erom ou3 uehiomwS -n1ethy1—3-hexene {ZJEZIBromo—I‘t ncllloro-S-mefltyl-3 -hexene {Z}—2—Brolno-3 -ch_loro-5-rnethyl—2-—hexe11e fE}—2wMethyI-5-bromo-4nchloro—4-hexene Which is a correct name for the following emnpound'? firm/CI I W (EJ-l -Bromc-l -eltloro~2+rnethyl- l -11exene (Z)-l-Brorno- l -ehIoro—2vrnethy1-1 -hexene (EJ-E-Brornoehloromethylenehexane (Z)-2-Bromochloromethylenehex one I2n[E,E)—Erontochlorometh}rl~H1exe ne Which statement(s) is (are) true of acid-catalyzed alcohol utlel'L:-,n:lrstions’iI Protonation ofthe alcohol is a fast step. Formation of a carbonation from the protonated alcohol is a slow step. Rearrangements of less stable carbocations to more stable carbccations are common. Loss ofa proton by the earhocation is a fast steP. All of the above 5. Which alcohol would initially produce the roost stair-locarbocatioo when trcatcd with , concentratcd H1304? . I a J".- in“ CH3C‘CH3CH3 3 £41,,th H do: C. “3-th ' E} C 1-13 | CH3CHCHCH3 I at C} CH3 ' | CH3CHCH3CH3 DH D} CH3 | HDCHzflHCHgCHg E) CH3 OH | CH3CHCH2CH3 5. Ncopcoryl alcohol, {CH3J3CCHgGl-L cannot ho dehydrated to an alkcnc without rcm‘raogcmcnt. What is the chicf product of dehydration? CHE—CH2 H \ _ \ _ / z ffiwi /C‘C\ CH2 [la-CH3 CH3 A CH3 (9 CH3 / \ IcH3 /H D \o—bo E / \ H CHE—"CH3 "I". What is the major product of the rcactioo1 CH3 Br I | (CHE J 3' CC“— CH3—C—CH—CH3 ———a '2 I (CH3) 3COH CH3 & A} {CH3J;C=C{CH;J3 @ (coahcacwom C) {CH3 )1C=CHCH3 I[}) {{3fi])1[:==(Tii(:flzfjfi3 E) Nonc of Tltcso 3. WI is the major product nfthe Following mactifln‘? .. 4:. LEI-Fa 5"“‘5 w ‘3 ‘I gin-{h 261}? / El CHE—CH2_‘:|3—Er + OH ——:- r? CH3 A) CHQECH-CHHCHg I CH3 H) CH3 | C’, CHE—CHE—C—DH | CH3 l CH3—CH=C-CH3 D] CH3 | CHgv-CHg-CHO—CH 2—CH3 CH3 E) {J CH3 GHQ—CHE—CH H CH3 9. Which would he the major product at" the £01113me reacfinn? I" CH3 5 “In ”3““ 11'0”} 1:11 O ——h- ‘ Pt D D CH3 {3; ® CH: 3 CH3 C D D H D H D H D CH3 E D H CH3 D U IE}. (,9 B} C} D] E} A) B} C) E) What will he the major product ofthc following _rcaction‘? 35% H3904 Q\ on: A1A1/u+jr“-q CH3 OH | l CH3—C———CH~CH3 | CH3 CH3 I CH3—C=C—CH3 | CH3 CH3 CH2=C—CH-CH3 | CH3 CH3 | CH3fiG—CH=CH2 | CH3 CH3 CH3 | | CHg—CH—CH-O—CH—C—CH3 CH3 CH3 CH3 [ CH3-CH-CH=CH—CH3 heat CH3 1 | CH3 ~ r 1 Thc structure of the product obtained fi'cm 2—hotync and Lia'CgHjNI-lg is: CH3 H ‘k f C=C o3 H 5NH H CHg=CHCH1C H3 dfsficiuioj ml?“ Want-Ht“ H1, 6-411“ch ‘1“sz “M shim 12 '3} C} D) E} 13. A] B) C) D) E M. 15. C Wlfich reaction would yield 2-bu1yne'? CHsC—C: N5. + Cflgflr —> .. ' CHgCHgBr + HCEC: "Na. ——>W J- lbw—M CH3: Na + HC=CCH3 ——> X. More than [me of [base Nane of these Your task 13 to cum-art 2~hmmubutane m l-hutane 1n highflst yield. Mich reagcnis would you use. 9 I; r' H KOH I. I ,_ 3:23:53... H..- a a v . w- CflgflflgflNa m 'F‘ mm m (CHflgmmcmhan 1': bfliki'fi bra-L. Which alkene i3 most stable? Wlfich alcphul wnuld he most Basil}.F dahydrated'? DH mgr“: ’30 {afloauhuj A WAC}! DH V $01469 D E 16. Which mechanistic 5th in the acid-catalyzed dahydmfiun Cf 3,3-di1ncth3rI—2vbutanul is the rate datum-fining strap? - H) CH3 CH3 | I CH3—C—CH—CH3 + H3C’r xi CH3—C——CH—CH3 + H3:- | | | I CH3 CH CH3 CH3 3th I. + 69 H C CHg—C—CH—Cfig v4— CHg-C—CH-CHQ + H20 | | | + fl (5 CH3 CH2 CH3 gffiwfirfrufi h’F CFELDHCH'},3J~1 Step2. + {3} CH3 CH3 | I CH3-C-CH—CH3 # CHg-CrCH—CHg | + + I Step3. CH3 CH3 D} CH3 | CH3—C—CH—CH3 + H30 # (CH3)2C=CI[CH3:IZ + H3C+ + | Sle'p4. CH3 1?. For which 31km: docs sis. nCl equal (g) or trans not equal [E]? 3} CH3 CH2 CH3 ‘k r’ C=C I ‘~. H H H} CH3 Cl R 2’ C=C I \ Cl CH3 E 'r.’ E 1: 6) x = m E W: C, 6 C3 “ I H D) Cl B r R r‘ C: I R E‘ F E} C HECHZ CCCH “a I Cam” I R IE What characteristiefs} of all-types would make it difficult to prepare cyclohexyne'? @ The requirement for linearity at the triple bond center The large electron density between carbons of a triple bond C} the short carbon-carbon triple bond length Pp D) The need that the carbon carbon triple bond be internal in the chain E) E is wrong; don’t pick it! i! I 1,115 l ‘3: l3“ /"\ {Earn 19. 0 || What 1s theo structure of the compound X that yields 2 mol of formaldehyde HIGH} and ll ll 1 nrol ot' HCCHECH upon ozonolysis folloWed by treatment with zinc? l 03 ) If II II -——h— 2} Earl-13C! 2 ”C“ + HCCHECl-l d MM a a 23. The addition of bromine to cyclohexene would produce the conrpoundts) represented by structurets}: m“ H [Ma Efifils Evil? 3’ it. I A] Ialone l3 llalone C, C} llandlll Illalone E] I and ll 21. 22. A) E} D) E} Wt would be the major product offlto following roaotion? oHa o‘t CH3 CH3 CH3 GI CI ' CI or WHY—'41 'n. Hit-”'1 HCI I *1? CI What is the chief product of the acid-catalyzed hydration of 2—mothyl-2—butono'? CH3 I CHQCHCHECHEDH CH3 CH3CHCHCH3 | or; OH I {CH332CCH2CH3 CH3 | Hocrtg CHE H2 CH3 CH3 | Cch-CHCHg || Ho out o. \ (_-—-C..:‘1—" 9 f I‘ l (J l’t E h l H b\ (I) as am , 3H \‘fl 23. What would be the major product of the following reaction? Br: 1" H20 ——.3.. DH fiElr Br Br DH 24. Hydroxylation of gfi-E-butene with cold alkaline 0304 yields .a---'-—" E \i t\ HO OH t t HH‘H‘CLCHJCHE CH3 a. H Ho Q‘H \ _: wo—o H“! \ CH3 o 2:7. Markovnilrov addition of HE] to propene involves: initial attack by a chloride ion. initial attack by a chlorine atom. iaomerization of lichloropropano. --"1 A} B} ‘3} / formation of a propyl cation. (:35 Formation of an iaopropyl cation. " " "‘ —— _ _ _______ Y 9 no the K) ...
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